Ring Fission of Quinazolines by Means of the Reissert Reaction

元データ 1984-09-25 社団法人日本薬学会


Under the Reissert reaction conditions, quinazoline (1a) afforded 2'-formylbenzanilide (2a), o-aminobenzaldehyde (3a), and N-formylbenzamide (4). Similarly, 4-methyl-(1b) and 4-ethoxyquinazoline (1c) gave the corresponding benzanilides 2b and 2c, respectively, o-aminoacetophenone (3b, from 1b), and benzamide (5). It was confirmed that the same results were obtained in the absence of the cyanide ion. A substituent at the 2-position prevented the ring fission, and only the corresponding N^3-benzoyl pseudo-base (14) was obtained. The generality of the ring fission was shown by the reactions of 1-phenyl-1H-pyrazolo [3,4-d] pyrimidine (6) and 3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine (8), giving 5-amino-1-phenyl-1H-pyrazole-4-carbaldehyde (7) and 5-amino-1-phenyl-1H-1,2,3-triazole-4-carbaldehyde (9), respectively.


五島 綾子 Shizuoka College Of Pharmacy
小久保 宏恭 Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
林 英作 Shizuoka College of Pharmacy
東野 武郎 Shizuoka College of Pharmacy
林 英作 School Of Pharmaceutical Sciences University Of Shizuoka
小久保 宏恭 Shizuoka College of Pharmacy
竹元 万寿美 Shizuoka College of Pharmacy